Yellow polyester fabric material and dyeing process therefor

ABSTRACT

WHEREIN: X is hydrogen, chloro or lower alkyl; Y is hydrogen or lower alkoxy; Z is hydrogen, chloro or lower alkoxy; R1 is hydrogen, lower alkyl or phenyl; R2 is hydrogen or lower alyl; R3 is hydrogen or methyl; R4 is cyano, lower carbacyloxy, chloro(lower carbacyloxy) or benzoyloxy; and R5 is cyano, lower carbacyloxy, chloro(lower carbacyloxy) or benzoyloxy, or when R4 is benzoyloxy, R5 may be hydrogen. The above compounds are made by diazotizing an aminobenzamide and coupling the resultant diazonium salt with a tertiary amino base having cyano-lower alkyl or esterfied hydroxy-lower alkyl groups attached to the tertiary amino nitrogen. The dyeings particularly on polyethylene terephthalate fibers, are of a bright yellow shade and are substantive, light fast, and sublimation resistant.   Synthetic fabric materials, particularly polyester fabric materials, are dyed a yellow shade through the use of monoazo dyes of the formula:

United States Patent 1191 Renfrew et al.

i541 YELLOW POLYESTER FABRIC MATERIAL AND DYEING PROCESS THEREFOR [75]Inventors: Edgar Earl Renfrew; Dominic Andrew Zanella, both of LockHaven, Pa.

[73 Assignee: American Aniline Products, Inc., Paterson, NJ.

[22] Filed: Feb. 5, 1973 [21] Appl. No.: 329,892

Related US. Application Data [63] Continuation-impart of Ser. No.80,171, Oct. 12,

1970, abandoned.

52 U.S. c1 8/41 0, 260/207, 260/207.1 51 int. Cl D06p I/l8 5 Field ofSearch 8/41 0; 260/207, 207.1

[56] References Cited UNITED STATES PATENTS 1,975,160 10/1934 Jordan etal. 260/207.1 2,941,992 6/1960 Rhyner et al. 260/205 3,050,516 8/1962Morian etal..." 260/205 3,268,507 8/1966 Kruckenberg 260/207 3,536,69510/1970 Groebke 260/207.l

Primary Examiner-Thomas J. Herbert, Jr Attorney, Agent, orFirm-Armstrong & Wegner 1 1 ABSTRACT Synthetic fabric materials,particularly polyester fabric materials, are dyed a yellow shade throughthe use of [1111 3,801,270 11 Apr.'2 1974 monoazo dyes of the formula:

The above compounds are made by diazotizing an aminobenzamide andcoupling the resultant diazonium salt with a tertiary amino base havingcyano-lower alkyl or esterfied hydroxy-lower alkyl groups attached tothe tertiary amino nitrogen. The dyeings particularly on polyethyleneterephthalate fibers, are of a bright yellow shadev and are substantive,light fast, and sublimation resistant.

6 Claims, No Drawings YELLOW POLYESTER FABRIC MATERIAL AND DYEINGPROCESS THEREFOR CROSS REFERENCE TO RELATED APPLICATION This applicationis a continuation-in-part of our copending application, Ser. No. 80,171,filed Oct. 12, 1970, now abandoned.

BACKGROUND OF THE INVENTION dyed by conventional methods on for example,polyethylene terephthalate, are acceptable in all of the importantphysicalproperties of substantivity, light fastness and resistance tosublimation. The standard of performance required with respect to thesephysical properties has become increasingly. critical because of thedemands of the textile industry. Recent'standards are such that somedyes which were considered acceptable several years ago are now regardedas unsuitable and have been replaced in the market by dyes of betteroverall performance. 3 I

Comparatively few monoazo dyes have been made from diazotizedaminobenzamides. Jordan et al., in US. Pat. No. 1,975,160, disclose aseries of such dyes made by diazotizing aminobenzamides and couplingtheminto N,N(di-lower alkyl) anilines. The dyes of Jordan et al are reportedto have excellent affinity for cellulose esters and satisfactoryfastness to light and washing on, for example, cellulose acetate.However, such dyes when applied to polyester textile material givedyeings which are only fair to poor in sublimation resistance,particularly at high temperatures.

Polyester textile material is conveniently dyed with dispersed dyes bycarrier dyeing, pressure dyeing, and by thermofixation methods. such asthe Thermosol process. An important characteristic of a commerciallysuccessful'dye for polyesters relates to the ability of the dye to buildup in strength on the fabric in proportion to the amount of dye applied.A dye should also color polyesters with little or no variation in shaderegardless of the particular dyeing method used.

Although it is known that higher molecular weight dyes generally providedyeings of better physical prop erties, the use ofa high molecularweight coupler often seriously impairs the ability of the resulting dyeto build in strength on polyester fabric in proportion to the amount ofdye applied. This problem is encountered when using dyes such as thosedescribed in US. Pat. No. 3,268,507 in which aminobenzamides are amongthe bases diazotized and coupled into dihydroxyalkyl substitutedtertiary amino coupling components, the hydroxyl groups of which havingbeen reacted with a lower alkyl chloroformate to form carbonate esters.These dyes are suitable for dyeing for thermofixation and carrier dyeingmethods, but do not build up on polyester fibers when applied by thepressure dyeing v 2" fibers and which build in strength when applied byany of the conventional dyeing methods.

SUMMARY OF THE INVENTION In accordance with a first aspect of theinvention, there are provided synthetic fabrics dyed in a bright yellowshade.

In accordance with a second aspect of the invention, there is provided anovel class of monoazo dyes of the form a CHRaCI'IzR bacyloxy) orbenzoyloxy or when R is benzoyloxy, R5 may be.v hydrogen.

In accordance with a preferredembodiment of this second aspect of theinvention, there are provided a novel subclass of monoazo dyes of theabove formula:

wherein: W

X is hydrogen, chloro or lower alkyl; Y is hydrogen or lower alkoxy; andeach of V and W is independently cyano of acetoxy. As preferred loweralkyl groups may be mentioned methyl, ethyl, propyl and butyl,particularly methyl and ethyl. As preferred lower alkoxy groups may bementioned methoxy, ethoxy, propoxy and butoxy, particularly methoxy andethoxy. By the terminology lower carbacyloxy is contemplated thegrouping Cl -4 alkyl)- COO, acetoxy being a particularly preferredembodiment. By the term chloro(lower carbacyloxy) is contemplatedchloro( Cl 4 alkyl)COO OQ-, partiwlarly chloroacetoxy. Preferably thecarbarnyl group is para or meta to the azo group of the monoazo dyes(I); in

a particularly preferred embodiment the carbarnyl group 'is meta to theazo group.

The monoazo dyes (I) when applied to synthetic polyester textile fiberin an amount such that the colored fiber contains about 0.1-2 percent byweight dye, provide colored flb6I'S of bright yellow shades havingoutstanding sublimation characteristics as well as good substantivity.The monoazo dyes (I) build up well on 4-aminobenzamide;

' acetoxyethyl)-N-(2-cyanoethyl )aniline; I

DETAlLED DESCRlPTlON The monoazo dyes (l) are made by conventionalmethods involving diazotizing an aminobenzamide and coupling theresulting diazonium salt with (1) an N,N- bix (2-lower acyloxy loweralkyl)aniline, either unsubstitut ed or appropriately substituted withchloro, lower alkyl or lower alkoxy groups; (2) an N,N-bis (2-cyanolower alkyl)aniline, either unsubstituted or appropriately substitutedwith chloro, lower alkyl or lower alkoxy groups; (3) N-(Z-lower acyloxylower allcyl)-N(2- cyano lower alkyl)aniline, either unsubstituted orappropriately substituted with chloro, lower alkyl or lower alkoxygroups; and (4) benzoylated N-lower al kyl-anilino lower alkanols,either unsubstituted or appropriately substituted to correspond to X andY in the formula given above. Gther variations of coupling components inwhich different groups are attached to the tertiary amino nitrogen areevident from the above formula.

Useful bases include 3 3-amino-4-chlorobenzamide;4-amino-2-chlorobenzamide; 3-amino4-methoxybenzamides; 3-amino-4-chloro-.N,N-.dimethylbenzamide; ,3-amino-N-ethylbenzamide; '3-aminobenzanilide; 3-amino-4-chloro.-N,N-di(2- cyanoethyn benzamide;4'-amino-3-chlorobenzanilide; 4-amino3-chlorobenzamide;4-amino-3-chloro-N-(npropyl)benzamide. v

Typicaluseful couplers are N,N-bis(2-acetoxyethyl) aniline}N,N-bis(2-cyanoethyl)aniline; I N-(2- N-(2-benzoyloriyethyl)N-ethylaniline; N,N-bis(2-acetoxyethyl)-"m-toluidine;N,N-bis(2-cyanoethyl)-ni-toluidine; N-(Z-propionyloxyethyl)N-(Z-CyanoethyD-mtoluidine; N,N-bis(2-acetoxyethyl)-5-methyl-oanisidine;N,,N-bis(2cyanoethyl) -m-chloroaniline; N[-2-(n-butyrylo'xy)ethyl]-N-(2-cyanoethyl)-ov phenetidine. I

The base is diazoti'zed by any conventional method, for example, in the'case of 3-amino-4- chlorobenzamide, the benza'mide is first dissolvedin dilute hydrochloric acid; The solution is 'iced in O" C andsufficient'sodium nitrite is added to form the diazonium salt at atemperature below 5 C; Diazotization is complete in about on eihour andexcess nitrite can be removed with sufficientsulfa nic acid. The diazosolution is filtered, and the filtrate is kept cold forcoupling. I

The coupling components can be made by any suit- ;able process such asby the conventional esterification filtration and the filtered cake iswashed with water until the washings are acid-free.

The monoazo dye (I) may be standardized either as a disperse pasteor adispsese powder by any of the basic standardizing techniques that havebeen known 4' to the art for many years; i.e., by the use of appropriateamounts of commondispersants and standardizing agents, usually togetherwith small amounts of anionic wetting agent'to assist in dispersion.

Standardized pastes are made by wet milling the dye in conventionalequipment in the presence of a dispersing agent, preferably sodiumlignin sulfonate or sodium alkylnaphthalene sulfonate. Various othercommercially available dispersing agents, such as sodium salts ofcarboxylated polyelectrolytes and the naphthalene sulfonates; e.g., thecondensation products of sulfonated naphthalene and formaldehyde, suchas sodium dinaphthylmethane disulfonate, are conveniently used. Thedispersed paste may be cut or standardized to a standard strength withwater. The final color content of the finished paste averages from 10-40percent by ized if necessary to provide the dispersed powder. The

color is cut or standardized to a standard strength in a blender with adiluent,zsuch as sodium sulfate or dextrin. A wetting agent, such assodium cetyl sulfate or'an alkylphenoxy polyethanol may be'added to wetout the product. Dispersed powders are usually cut or standardized to26-60 percent by weight color content (pur ecolor). The monoazo dyefl),when added to water with or without auxiliary agent's, forms a nearcolloidal aqueous dispersion from which the aromatic polyester fiber ortextile material is dyed in the conventional manner at 40100 C (l04"212F) to give a colored fiber containing about 0. 0l2 percent by weight dye(100 percent color basis).

Alternatively, dyeing may be accomplished without a carrier attemperatures of l00-l'50C under pressure. Also, the dye may be appliedin patterns by conventional printing methods, if desired.

The monoazo dye (I) can also be applied to the aromatic polyester fiberby thermofixation methods, such as the Thermosal process. This. process,which involves padding the cloth with the diluted dye dispersionfollowed by drying and heatingthe dried goods with hot air or heatedcontact rolls, is conveniently used for dyeing polyester fibers andblends containing these fibers. Temperatures of l220 C (ca. 360-425 F)are used for 30 to seconds. If the fabriccontains cotton or viscoserayon, apart from synthetic fibers, there is no danger of damagingcellulosic portions, but if wool is present, the temperature must bekept within l80200 C and the time must be reduced to 30 seconds.

in order to evaluate the effectiveness of a particular dye for a giventype of fiber, the dyed fiber is examined for substantivity of thecolor, light fastness of the color, and resistance of the color tosublimation. Specific tests for the evaluation of these importantproperties are described in the examples that follow.

Example 1 A. Diazotization To a 1 liter beaker was charged 120 ml. hotwater, 60 g. hydrochloric acid (32 percent by weight) 34.1 g.3-amino-4-chlorobenzamide and 5 g. Tween 20, (a commercially availablesurface active material said to be polyoxyethylene sorbitanmonolaurate). The mixture was stirred until the solids were dissolved.The solution was cooled to 0 C by the addition of ice. To the stirredsolution at 05 C was added dropwise over 1 hour a solution of 14.0 g.sodium nitrite in 35 mil. water. Stirring was continued for one morehour at O5, during which time a slight excess of nitrite was maintainedby small additions. At the end of the period, the excess of nitrite wasremoved with sufficient sulfamic acid. The cold solution was filteredand the filtrate kept cold.

B. Coupler To a 500 ml. flask was charged 50.0 g. glacial acetic acidand 370 g. 2,2-(phenylimino)diethanol. The solution was heated to 95 C.To the stirred solution at 95-l00 C was added slowly 42.0 g. aceticanhydride. After the addition, stirring at 95l00 C was continued 1 hour.The contents of the flask were then poured into a 3 liter beakercontaining 600 g. ice, 1,500 ml. water, and g. hydrochloric acid (32percent). The mixture was stirred one-half hour.

C. Coupling Ice was added to the solution B to bring the temperature to0 C. To the stirred solution was added in a slow stream the solution A;the temperature was maintained at O5 during the addition. Then was addedslowly a I solution of 45.0 g. sodium acetate in 225 ml. water.

The mass was stirred for sixteen hours during which time its temperaturewas allowed to rise to that of the surroundings.

The precipitate was collected on a filter and washed with water untilthe washings were no longer acidic. The cake after drying at 80 Cweighed 85.2 g. D. Dispersion To a ball mill of suitable size wascharged 60 g. of the dried product C, 60 g. Marasperse N-22(acommercially availablesodium ligninsulfonate) and 280 ml. water.Milling was continued until a satisfactory dispersion had been reachedas shown by a rate-of-filtration test. E. Dyeing and Testing An aqueousdye bath containing 10 percent Marcron L (a commercially availablephenolic dye carrier) and 1 percent monosodium phosphate as a bufferingagent was prepared. Type 54 Dacron polyester fabric was treated in abath at 120 F for 10 minutes, the fabric to water dye bath ratio being1:40. The dispersed dye paste D was added in an amount sufficient toprovide a bath containing 2 percent dye based on the weight of polyesterfiber. Dyeing was continued for one hour at 205 F and the fabric wasremoved from the bath, rinsed and dried. The hue was a bright goldenyellow.

Sample dyeings were tested for sublimation according to standard'AATCCColor Fastness to Dry Heat terized by excellent sublimation even attemperatures of 400 and 425 F. I

Similar excellent results were obtained when the dye was applied to thefabric by the Thermosol process and the pressure dyeing method and thentested for sublimation as described above. The build-up on the fiber inboth cases was also excellent.

The dyeings were also tested for light fastness by subjecting them tocarbon are fading in accordance with AATCC Color Fastness to Light:Carbon Arc. Lamp, Continuous Light Test No. l6A-l964. The dyeings showedonly a very slight break at 20 hours exposure indicating adequatefastness to light.

Example 2 c1 N=NNwmomoooomn ONH: H3

A. Diazotization A solution was prepared exactly as described in Example1, Part A. B. Coupler In the manner of Example 1, Part B, butsubstituting 40.0 g. 2,2-(m-tolylimino )diethanol for the 2,2-(phenylimino) diethanol, a coupler solution was prepared.

C. Coupling The solutions A and B were combined in the manner describedin Example 1, Part C. The yield of dried product was 84.0 g.

D. Dispersion 1 The product C was dispersed in the way described inExample 1, Part D. The paste obtained was spray dried, yielding a powderwhich was 50 percent dye and 50 percent dispersing agent.

E. Dyeing and Testing I The powder, D, was applied to polyesterterephthalate fibers in the ways referred to .in Example 1, Part E. Thehue-was yellow, but somewhat redder than the material of Example 1.Performance properties were simi-- larly good.

A Example 3 H CH3 N=NN cmd'nooocm 1 o morn) 1 A. Diazotization By thesame procedure given inExample 1, Part A, there was diazotized 39.7 g.3-amino-4-chloro-N,N- dimethylbenzamide. B. Coupler A coupler solutionwas prepared in the way described in Example 1, Part B, ,except that42.0 g. 2,2- (phenylimino)-dipropanol was used instead of 2,2-(phenylimino)diethanol. C. Coupling The materials A and B were combinedin the same way described in Example 1, Part C. The yield was 90.0 V

in the way described in Example 4 A. Dia zotiiation To a lliter beakerwas charged 150 ml. hot water, 60 I g. hydrochloric acid (32 percent).and 42.2 g. 3- aminobenzanilide. Stirring wasv carried on until thematerial was dissolved. To the stirred solution at 5 C wasadded slowlyover one hour a solution of 14.0 g. so-

dium nitrite in 40 ml. water. The diazotization mass was stirred foranad'ditionalhour at 0-5 C, during which time a slight excess of nitritewas maintained. At the end of the period, the excess of nitrite wasremoved by I the addition of sufficientsulfamic acid; The cold solutionwas clarified through a bed of diatomaceous earth filter aid, andpreserved cold for use in C. B.'Cou pler V A coupler solution was madein exactly the way described in Example 1, Part B. y

C. Coupling I The solutions A and B were combined in essentially themanner detailed in Example 1, Part C. The filter cake was not dried. Adry test indicated that aproximately 96 g. product had been obtained. D.Dispersion Wet cake C-containing a calculated 50 g. was dispersed in aball mill with 50 g. sodium ligninsulfonate I (a commercial grade,Marasperse N-22 was used) adequate filter test had been Example wascontinued for another hour, during which time the A. Diazotization Asolution was made from 49.3 g. '3-amino-4- chlorobenzanilide in themanner described in Example 4, Part A for 3-aminobenzanilide. B. CouplerA solution was prepared exactly as described in Example I, Part B. C.Coupling The combination of the solutions A and B was carried out asindicated in Example 4, Part C. Theyield was 96 g. isolated as moistcake.

. D. Dispersion I A disperse paste was made in the way defined inExample 4, Part D. E. Dyeing and Testing Polyester fabrics dyed with thepaste D in the conventional ways were golden yellow in hue. AATCC testsshowed remarkable resistance to sublimation. The dye is particularlysuited to application'by thermofixation methods.

E ms! A. Diazotization A solution was made in the way described inExample 1,PartA. B. Coupler A 1 To a 500 ml. flask was charged 60 g.propionic acid and37.0 g. 2,2'-(phenylimino)diethanol. The stirredsolution was heated to C, at which temperature 55.0 g. propionicanhydride was run inslowly. Stirring temperature was maintained above 95C. The solution after cooling somewhat, was then poured into a 4-literbeakercontaining 400 g. ice, 3,500 'ml water and 25 g. hydrochloric acid(32 percent). The mixture was stirred for another hour before use in thecoupling. C. Coupling I The solutions A and B were combined in themanner described in Example 1, Part C. The indicated yield of dyecon'tained in the moist cake was 87 g,

D. Dispersion I I 3 The product C was dispersed to a 50 percent powderin the way described in Example 2, Part'D.

E. Dyeing and Testing Dyeing and testing were carried out as indicatedin Example 2, Part E. The dyed polyester material looked and performedmuch like the dyed goods of Example I, Part E.

A. Diazotization I A solution was made in the way described in Example1, Part A.- 1 B. Coupler To a 500 ml. flask was charged 50 g. glacialacetic acid, and 45.5 g. 2,2'-(6-methoxy -mtoiylimino)diethanol. To thestirred solution at 95-100 C was added slowly 45.0 g. acetic anhydride.Stirring at 100 C was continued for 1 hour after the addition had beencompleted. After cooling somewhat the contents of the flask were pouredinto a 3 liter beaker containing 400 g. ice, 3,500 ml. water and 25 g.hydrochloric acid (32 percent). The solution was stirred for one-halfhour.

C. Coupling The solutions A and B were combined in the way described inExample 1, Part C. An indicated yield of 88 g. was obtained as wet cake.

D. Dispersion The cake D was dispersed to a 15 percent paste in the waydescribed in Example 1, Part D.

E. Dyeing and Testing Standard dyeing methods and AATCC testingprocedures were carried out in the manner indicated in Example 1, PartE. Hues were reddish-orange. Properties were good, with resistance tosublimation outstanding.

A. Diazotizationv A solution Part A.

B. Coupler To a 500 ml. flask was charged 60.0 g. chloroacetic acid and44.8 g. 2,2'-(o-ethoxyphenylimino)diethanol. The mass was heated untilit became stirrable, ca.60 C. At 80-86 C, while stirring, was added over1 hour 47.0 g. chloroacetyl chloride. After the addition, the mass wasstirred 1 hour at 80 C, cooled somewhat and drowned into a 2 literbeaker containing 800 ml. cold' water, 200 g. ice, 40 g. hydrochloricacid 32 percent) and 2 g. Tween 20, a commercially available materialsaid to be a polyoxyethylene sorbitan monolaurate. The drowning mass wasclear.

C. Coupling Combiningof the solutions A and B was carried out inessentially the way described in Example 1, Part C; A yield of 104 g.was obtained as moist filter cake.

D. Dispersion A 15 percent paste was prepared in Example 1, Part D.

E. Dyeing and Testing Fabric samples dyed in the ways indicated inExample 1, Part E were subjected to test procedures recommended byAATCC. Properties were very good; subli-' mation fastness wasexceptionally good. The hue was orange.

in the way detailed Example 9 Cl I CIIiCHflOCOCH2Cl -N=N N (E CHaCHzO-COONHCIIJ was. prepared exactly as in Example 1.,'

To a 500 ml. flask was charged 75.0 g. chloroacetic acid and 30.0 g.benzoyl chloride. The mixture was heated to 65 C over one-half hour atwhich temperature 36.6-g. 2,2-(phenylimino) diethanol was added to thestirred mass. A slight rise in temperature took place during theaddition. Stirring at 70 was continued for 3 hours. The charge was thenpoured into a 2 liter beaker charged with 200 g. ice, 200 ml. coldwater, 40.0 of hydrochloric acid (32 percent) and 5 g. Tween 20, (acommercially available polyoxyethylene sorbitan monolaurate). Stirringwas carried on for one hour more, after which the solution was clarifiedthrough a diatomaceous earth filter bed.

C. Coupling The combining of the solution A and B was carried out asdescribed in Example 1, Part C. Approximately 88 g. was obtained asmoist cake. Thin layer chromatography showed the presence of severalcomponents, of which the structure given is probably'a major one. D.Dispersion The cake C was dispersed to a percent paste in the mannerdescribed in Example -1 Part D.

E. Dyeing and Testing Dyeings were made in'the manner indicated inExample 1, Part E, and tested by AATCC methods. The hue was goldenyellow. Properties, especially fastness to sublimation, were very good,

Example 10 cmcmooo A. Diazotization A solution was ample 1, Part A. B.Coupler i To a 500 ml. flask was charged 33.0 g. 2(N- ethylanilino)ethanol. To thismate rialat 70-80 C was added alowly 28.0 g. benzoylchloride. The mixture was stirred at 7080 C for 2 hours, after which itwas heated to 90 C. The mass was poured-slowly into a' stirred mixturemade of 400 g. ice, 400 ml. water, 25 g. hydrochloric acid, .32 percentand 5 g. Tween 20, a commercially available surface active material. Thedrowning mixture was stirred for one more hour.

C. Coupling The solutions A and B were combined in essentially the waydescribed in Example 1, Part C. The yield of dried cake was 73.0 g. D.Dispersion prepared exactlyas described in Ex- A paste of 15 percentcolor content was made by milling theproduct C with a dispersing agentand water in the way described in Example 1, Part D. E. Dyeing andTesting Polyester fabric was dyed by the several methods noted inExample 1, Part E. Tests conducted by AATCC specification showed thepresent dye to have excellent fastness properties. sublimation fastnessis remarkably good. The hue is golden yellow.

Examples 11 to 17 By procedures essentially as given in Example 1 to 10,bases and couplers give dyes as tabulated.

13 V Example 18 O NH:

A. Diazotization A solution was prepared exactly as described in Example1, Part A.

Ice was added to the coupler solution (Part B) until I the temperaturewas 0 C. The clarified diazonium solution-from Part A was slowly addedtothe stirred coupler solution; ice was added as needed to maintain thetemperature at 05 C. After the addition was complete, stirring wascontinued for four hours during which the temperature was maintained at0-5 C, and

ten hours during which time it was allowed to rise spontaneously to thatof the room. The solid couplingproduct was then isolated by filtration,washed acid free on the filter, and dried. l't weighed 69.6 g.

D. Dispersion A percent color content disperse paste was preparedexactly as described in Example 1.

E. Dyeing and Testing Golden-yellow dyeings were prepared in the mannerdescribed in Example 1. Properties were excellent. The dyestuff isespecially suited for dyeing by the thermofixation method, yieldingdyeings of outstanding sublimation and good light fastness.

The foregoing dyes also color cellulose triacetate in good shades ofexcellent fastness. Many of them, especially the dyes of Examples 1-, 2,6, ll, 14 and 15, also wherein:

X is hydrogen, chloro or lower alkyl;

Y is hydrogen or lower alkoxy;

Z is hydrogen, chloro-or lower alkoxy;

R, ishydrogen, lower alkyl or phenyl;

R is hydrogen or lower alkyl;

R is hydrogen or methyl; E

R is cyano, lower carbacyloxy, chloro(lower carbacyloxy) or benzoyloxy;and

R is cyano, lower carbacyloxy, chloro(lower Icarbacyloxy) or'benzoyloxy, or when R., is benzoyloxy, R may be hydrogen.

2. The dyed material of claim 1 wherein said aromatic polyester fabricmaterial is polyethylene terephthalate. I

3. An aromatic polyester fabric material of claim 1 wherein saidcompound is of the-formula:

4. An aromatic polyester fabric material of claim 3 wherein saidcompound is of the formula:

CONHz 5. An aromatic fabric material of claim 3 wherein said compound isof the formula:

yield dyeings of excellent properties on secondary cellulose acetate.

What is claimed is: 1. An aromatic polyester fabric material dyed with acompound of the formula;

l CHR CHR (3 0 X l I a. N

6. ,An aromatic polyester fabric material of claim 3 wherein saidcompound is of the formula:

CHzCHzCN 0 ONE:

2. The dyed material of claim 1 wherein said aromatic polyester fabricmaterial is polyethylene terephthalate.
 3. An aromatic polyester fabricmaterial of claim 1 wherein said compound is of the formula:
 4. Anaromatic polyester fabric material of claim 3 wherein said compound isof the formula:
 5. An aromatic fabric material of claim 3 wherein saidcompound is of the formula:
 6. An aromatic polyester fabric material ofclaim 3 wherein said compound is of the formula: